R. Duke, M. Chebib, D. Hibbs
Jun 7, 2004
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0
Influential Citations
11
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract E-4-Amino-2-methylbut-2-enoic acid, (±)-4-amino-2-methylbutanoic acid, (+)-(S)- and (−)-(R)-4-amino-2-methylbutanoic acid, which are analogues of the inhibitory neurotransmitter GABA (γ-aminobutyric acid, 4-aminobutanoic acid), were synthesised from ethyl 2-methyl-4-phthalimidobut-2-enoate, ethyl 2-methyl-4-phthalimidobutanoate, (+)-[(2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2S)-methyl-4-phthalimidobutanoate and (−)-[(2R-(3,3-dimethylbutyro-1,4-lactonyl)]-(2R)-methyl-4-phthalimidobutanoate, respectively. The assignment of the absolute configuration of (+)-(S)- and (−)-(R)-4-amino-2-methylbutanoic acid was based on the X-ray crystallographic structure of the (+)-(R,S)-diastereoisomer, and direct comparison of specific rotations with the published data for (−)-(R)-4-amino-2-methylbutanoic acid.